- "Why am I not surprised? Wherever Darhk is, you're not too far away."
- —Sara to Merlyn
"The Chicago Way" is the eighth and midseason finale episode of the second season of , and the twenty-fourth episode overall. It aired on December 8, 2016.
|When a new Time Aberration is discovered by the Legends, they find themselves headed to 1927 Chicago. The Legends quickly realize that they have been set up by Eobard Thawne, Damien Darhk and the newest member of the Legion of Doom, Malcolm Merlyn. While everyone is trying to help fix what they think is the mission, Jax encourages a reluctant Stein to share his secret with the other Legends. Stein is taken captive and Sara must make the tough choice of either stopping the Legion of Doom or saving Stein. Meanwhile, Rory gets an unexpected visitor and is not sure how to handle it.|
- Victor Garber as Professor Martin Stein/Firestorm and Professor Eobard Thawne
- Brandon Routh as Dr. Ray Palmer/The Atom
- Arthur Darvill as Rip Hunter
- Caity Lotz as Captain Sara Lance/White Canary
- Franz Drameh as Jefferson "Jax" Jackson/Firestorm
- Matt Letscher as Professor Eobard Thawne/Reverse-Flash
- Maisie Richardson-Sellers as Amaya Jiwe/Vixen
- Amy Pemberton as Gideon (voice)
- Nick Zano as Dr. Nate Heywood/Steel
- Dominic Purcell as Mick Rory/Heat Wave
Special appearance by
Special guest star
- Sean Campbell as Agent Cole Bennett
- Cameron Dent as Bartender
- Darryl Scheelar as Driver
- Dan Rizzuto as Goon
- Donal Thoms-Cappello as Police Officer
Thawne, Darhk and Malcolm arrive in Chicago, 1927, and ally with Al Capone.
The team get alerted by the aberration and arrive, managing to save Eliot Ness from getting killed by Capone. They put Ness in the care of Gideon and decide to complete his mission to secure history.
They infiltrate a club owned by Capone. Sara and Martin are abducted. He tells her about Lily. The team rescues the duo and brings them to the Waverider, where it is revealed that Thawne has imposed himself as Martin.
Thawne opens the door for Malcolm and Capone's operatives. Sara yields the amulet in exchange for Martin's location.
The latter is saved from Capone. Sara agrees not to erase Lily from the timeline. With the completed amulet, Thawne shows Darhk and Malcolm a hologram that is compass meant to help find the Spear of Destiny, which the former believes can be used to "rewrite reality itself".
He also states that they need to find Rip. The final scene shows that Rip is working as a movie director in Los Angeles, directing an actor who looks very much like Ray Palmer. in 1967.
Meanwhile, Mick starts having hallucinations of Leonard, who blames him for helping the team. Mick also starts becoming more intimate with Amaya.
Preparation ran from October 3 until October 12, 2016, with a break for Canadian Thanksgiving on October 10. Shooting ran from October 13 until October 24, 2016.
- The title of the episode is a reference to a quote from the 1987 gangster film The Untouchables, in which Jimmy Malone describes to Eliot Ness how to get Al Capone, describing it as "the Chicago way".
- When he's about to seemingly drown, Eliot Ness says his famous true line, "Never stop fighting until the fight is done!"
- While posing as an F.B.I. agent, Ray uses the alias "Bob De Niro". This is a reference to actor Robert De Niro, who played Al Capone in The Untouchables.
- Ray does an impression of Jimmy Malone (played by Sean Connery) with his line "Isn't that just like a thug? Brings a tommy gun to an ion blaster fight."
- It wasn't revealed which year Malcolm Merlyn is from in this episode. However, he was seen with his cybernetic hand, which means that this is a version of Malcolm Merlyn from some time after "".
- The device Eobard Thawne used to take the appearance of Martin Stein is the same device he used to take the appearance of Harrison Wells. This is the first appearance of the device since episode, "".
- When Nate states that he should be the one to impersonate Eliot Ness, Ray claims that he would be fit if the mission involved impersonating Brad Pitt.
- Jax tells Ray and Nate that "Stein's about to kill Sara in the library" (when Thawne had already disguised himself as Stein using the aforementioned device). Ray asks "with the rope or the candlestick?" which is a reference to the game Clue (known outside North America as "Cluedo") where players have to solve a murder, deducing which suspect is the killer, which room the murder happened in, and which of several potential weapons was used.
- This also implies that the board game might actually be on the ship.
- In real life, Ness didn't create the team to work with him until 1929, two years after this episode is set, although he did start working in Chicago in 1927.
- Meigs Field is shown on the map of Chicago, despite existing in neither 1927 nor 2016 in real life. It was built in 1948 and destroyed in 2003.
- In real life, the Port of Chicago is located on the Far South Side around 87th Street, not near Meigs Field as is shown on the map.
- Ray refers to the Bureau as the FBI. However in 1927, it was called the BOI, Bureau of Investigation. The name wasn't changed to Federal Bureau of Investigation until 1935.
- Ness did a great deal of damage to Al Capone's operations, but he was not directly responsible for successfully convicting Capone of tax evasion.
- Martin and Jax share a psychic connection, so there is no reasonable way Jax should have been fooled by an impostor.
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